Synthesis and characterization of 3,13-and 2,13-octadecadienyl compounds for identification of the sex pheromone secreted by a clearwing moth, Nokona pernix

• Published in: Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2006, Vol.70 (2), p.508-516
• Main Authors: Naka, H.(National Inst. for Agro-Environmental Sciences, Tsukuba, Ibaraki (Japan)), Nakazawa, T, Sugie, M, Yamamoto, M, Horie, Y, Wakasugi, R, Arita, Y, Sugie, H, Tsuchida, K, Ando, T
• Format: Article
• Language: English
• Subjects: Animals; ATRAYENTES SEXUALES; ATTRACTIF SEXUEL; Biological and medical sciences; CHEMICAL SYNTHESIS; ESPECTROMETRIA DE MASAS; ESPECTROSCOPIA RMN; FEROMONAS SEXUALES; Fundamental and applied biological sciences. Psychology; Gas Chromatography-Mass Spectrometry; Lepidoptera; Magnetic Resonance Spectroscopy; Male; MASS SPECTROMETRY; Molecular Structure; Moths - chemistry; Moths - metabolism; NMR SPECTROSCOPY; Nokona pernix; octadecadien-1-ol; octadecadienyl acetate; PHEROMONE SEXUELLE; RUBIACEAE; SESIIDAE; sex attractant; SEX ATTRACTANTS; Sex Attractants - chemical synthesis; Sex Attractants - chemistry; Sex Attractants - metabolism; Sex Attractants - secretion; SEX PHEROMONES; SINTESIS QUIMICA; SPECTROMETRIE DE MASSE; SPECTROSCOPIE RMN; SYNTHESE CHIMIQUE
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.70.508

Several geometrical isomers of 3,13- and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13- and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of [M - 18]sup(+) at m/z 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)- and (3Z,13Z)-isomers of 3,13-octadecadien-1-o1 in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted N. pernix males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August.